Cc1cc2ccc(OC(F)(F)F)cc2[nH]1.Ic1cccc(OCc2ccccc2)c1>C1COCCO1.CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C.CC(C)(C)[O-].O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1EN04773-50, _Buchwald coupling,_ ** _J. Med. Chem. 2009, page 3846-3854 (changed: solvent to dioxane and bromide to iodide)._** The indole from 4773-41, 1-(benzyloxy)-3-iodobenzene, Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 120 °C for 1h and ~40% conversion was observed on NMR. The reaction mixture was further heated at 80 °C for 16h and 40 h, see attached 1H-NMR for reaction progress. A comparison with 4773-51 shows that using dioxane or iodide gives a lower yield (slower reaction). Switching the solvent to toluene was explored in 4773-52. The reaction in this experiment showed that the Buchwald conditions worked. Reaction mixture was thrown away.
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